Cheap flights from Toronto to Chicago

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Toronto to Chicago flight comparison made easy

Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto to Chicago by changing tabs
Quickest
Cheapest
Porter Airlines
Porter Airlines
12 Sep.
YTZ
4:20 a.m.
Toronto Island airport
1h 45m
5:05 a.m.
MDW
Chicago Midway airport
Porter Airlines
15 Sep.
MDW
6:10 a.m.
Chicago Midway airport
1h 42m
8:52 a.m.
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
04 Nov.
YTZ
3:25 p.m.
Toronto Island airport
1h 47m
4:12 p.m.
MDW
Chicago Midway airport
Porter Airlines
08 Nov.
MDW
1:40 p.m.
Chicago Midway airport
1h 42m
4:22 p.m.
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
11 Dec.
YTZ
8:20 a.m.
Toronto Island airport
1h 50m
9:10 a.m.
MDW
Chicago Midway airport
Porter Airlines
15 Dec.
MDW
7:20 a.m.
Chicago Midway airport
1h 40m
10:00 a.m.
YTZ
Toronto Island airport
257 CAD
United Airlines
United Airlines
29 Aug.
YYZ
8:20 a.m.
Toronto Pearson Intl airport
1h 49m
9:09 a.m.
ORD
Chicago O'Hare Intl airport
United Airlines
11 Sep.
ORD
2:50 a.m.
Chicago O'Hare Intl airport
1h 28m
5:18 a.m.
YYZ
Toronto Pearson Intl airport
333 CAD
Air Canada
Air Canada
24 Aug.
YYZ
4:55 p.m.
Toronto Pearson Intl airport
1h 44m
5:39 p.m.
ORD
Chicago O'Hare Intl airport
Air Canada
06 Sep.
ORD
4:55 a.m.
Chicago O'Hare Intl airport
1h 36m
7:31 a.m.
YYZ
Toronto Pearson Intl airport
333 CAD
ANA
ANA
22 Sep.
YYZ
4:16 a.m.
Toronto Pearson Intl airport
1h 47m
5:03 a.m.
ORD
Chicago O'Hare Intl airport
ANA
27 Sep.
ORD
9:00 a.m.
Chicago O'Hare Intl airport
1h 37m
11:37 a.m.
YYZ
Toronto Pearson Intl airport
551 CAD

How to get the cheapest flight from Toronto to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight for your trip
WHAT IS THE CHEAPEST MONTH TO FLY TO CHICAGO?
February
The cheapest time of year to fly to Chicago from Toronto is February. The most expensive is January.
WHAT IS THE CHEAPEST DAY TO FLY TO CHICAGO?
Thursday
The cheapest day of the week is typically Thursday. The most expensive is typically Sunday
WHEN IS THE CHEAPEST TIME TO FLY TO CHICAGO?
at noon
Toronto to Chicago flights are approximately 111% more expensive in the evening than at noon
WHAT IS THE CHEAPEST AIRLINE THAT FLIES TO CHICAGO?
Porter Airlines
Porter Airlines, Air Canada, and Iberia are the most popular carriers operating from Toronto to Chicago
WHAT IS THE CHEAPEST ROUTE?
Toronto Island - Chicago Midway
Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices
WHEN IS THE CHEAPEST TIME TO BOOK A FLIGHT TO CHICAGO?
38 days before
The cheapest time to buy a flight from Toronto to Chicago is approximately 38 days before departure
60
Days before departure
0

Flight information for Toronto to Chicago

Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago
Fastest flight time 1h 44m The fastest flight from Toronto to Chicago takes 1h 44m.
Direct flights Every day Direct flights go from Toronto to Chicago every day.
Airports in Chicago 3 airports There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Toronto to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Toronto to Bloomington
Fastest flight time
4h 55m
Cheapest price
383 CAD
Toronto to Kalamazoo
Fastest flight time
3h 20m
Cheapest price
405 CAD
London to Chicago
Fastest flight time
4h 55m
Cheapest price
432 CAD
Kingston to Chicago
Fastest flight time
4h 54m
Cheapest price
601 CAD
London to Chicago
Fastest flight time
9h 57m
Cheapest price
1,211 CAD
View more

Flights from Toronto to:

Flights to Chicago from:

  • Toronto
  • Ontario
  • Canada
  • North America